4-Hydroxybenzaldehyde → 4-(1-Hexenyl)phenol

HRID 1739483

반응식

HRID 1739483 반응식
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH3:6].[Li]N([Si](C)(C)C)[Si](C)(C)C.[OH:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=1>C1COCC1>[CH:41]([C:40]1[CH:43]=[CH:44][C:37]([OH:36])=[CH:38][CH:39]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 2724565Pentyltriphenylphosphonium bromideHCID 178418261HCID 178418261, 화합물

생성물 1

HCID 538311814-(1-Hexenyl)phenol수율 85.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of pentyl triphenylphosphonium bromide (4.76 g, 11.5 mMol) in freshly distilled THF (40 ml) was added LiN(SiMe3)2 (1N in THF, 23 ml). The red solution was stirred at ambient temperature for 30 minutes then a solution of p-hydroxybenzaldehyde (1.06 g, 10 mMol) in THF (10 ml) added. The reaction was stirred at ambient temperature for 4 days, then partitioned between ethyl ether and dilute aqueous HCl (1N). The combined etherial extracts were washed with brine, dried (MgSO4) and evaporated. The crude oil was purified by chromatography (eluant: ethyl ether/hexane) to give 4-(1-hexenyl)phenol as a pale yellow solid (1.5 g, 85%).

후처리

  1. stirringThe reaction was stirred at ambient temperature for 4 days
  2. custompartitioned between ethyl ether and dilute aqueous HCl (1N)
  3. washThe combined etherial extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude oil was purified by chromatography (eluant: ethyl ether/hexane)

출처 및 근거

ORD 기록
ord-41a8bfd3c65d40f98b729cab42e5078f
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965741

연결된 노트

불러오는 중…